Hey, Roomie
by dbb93
Summary: After Bonnie informs Elena she won't be able to move in with her and Caroline in their new apartment in NYC, both girls are in a desperate race to find someone to take her place. In comes the oh so charismatic, Damon Salvatore. Elena's reaction to first seeing the devastatingly beautiful man? "Oh, shit."
1. Chapter 1

"Between the two of us, there is no way in hell we'll be able to afford this place!" Elena Gilbert yelled.

Ever since she had been woken up an hour before her alarm was due to go off by an unexpected and unwanted call from one of her best friends, Bonnie Bennett, she had been cranky.

**_Earlier that day_**

"I'm really sorry, Elena! But it's such a good opportunity, I can't just pass it up." said Bonnie.

Bonnie had applied months back for a job at some big PR firm in California. She knew Elena and Caroline (best friend number two) wouldn't be too pleased with her since they had it planned for years that as soon as soon as they completed their senior year of college they would all move in together somewhere in the Big Apple, New York City.

"Yeah, I get it Bon, I really do, but we've had this planned since freshman year of high school!" Elena said, hoping the guilt card would work in her favor.

"I know, I know, but come on, Elena. It's my dream job, you of all people should know this feels."

And she did. Both Elena and Caroline had jobs waiting for them in New York. All throughout high school, Elena had sent every single one of her writings to a big time publishing company there, in the hopes they would take her seriously for when she was ready to apply for an action position. Her crazy/brilliant idea had paid off because the head of publishing had agreed to make Elena a member if she could produce a best selling novel by the end of the year. Caroline on the other hand had more girly aspirations. Hair stylist. And she was actually pretty damn good.

"Your right. This is a one in a lifetime opportunity for you. Go for it, Bon. I'm proud of you."

**_Back to present_**

Being the optimist that she is, Caroline proposed an idea, "Relax, 'Lena, we'll just find another roomie. I mean, come on, look at this view. It's beautiful! There is no way we won't be able to find someone else."

Elena walked over to the window, sighing the whole time.

"I hope your right, Care."

* * *

Both girls had moved in and started their new jobs, also promising to be on the look out for any potential room mates.

While at the Publishing house, Elena met a lot of great people, especially Alaric Saltzman.

"I know, it's a fucking bizarre name. Just call me, Ric." he said humorously.

"Hahaha, okay, Ric, so what's your story?"

"Whoa, jumping right in, are we? Okay, well I am 29, I live in Brooklyn, I love long walks on the beach and I'm a Pisces." he said with a grin.

"Wow, have you ever thought about writing an autobiography?" Elena teased.

"If you must know, yes, I have and it will be a best seller and no I will not give you a shout out in it." he said while trying to look serious.

Neither of them could keep up the charade any longer and they both started busting out laughing.

"Hey, a bunch of the employees here are going to some bar after work, you should tag along. It'll be a good way to meet the rest of the crew and spread the word about my much anticipated book." Ric said with a smile.

"Hmm, well I guess I could take some time out of my very, very, very busy schedule and join you." Elena said while pretending to page through her appointment book.

She already knew Ric was a great guy, and he might be right up Caroline's alley. He was definitely a good looking guy with her sandy brown hair, dark blue eyes, and from what Elena could see through his clothes, I very nice athletic build. Oh yeah, definitely Caroline's type.

The two of them spent the next hour talking and getting to know each other better. Elena had mentioned her and Caroline's current room mate problem and Ric told her he might have someone who could fix that problem.

"He'll be at the bar tonight as well, and you can decide then if he's maybe a serial killer or not.

After that, Ric stood up, threw on his sunglasses and said, "I think it's about time we get our drink on."

"Hahahaha, okay Mr. I-Wear-My-Sunglasses-At-Night, let me just call my friend and see if she can meet me there so we can both talk to this guy."


	2. Chapter 2

The bar had a cool city vibe to it, but not too intimidating for the two Southern bells. Caroline had already hit it off with Ric, just as Elena thought she would. The two were sitting at the end of the bar talking and laughing. It was really great seeing Caroline with a good guy, especially since she seemed to have a knack for attracting douche bag jocks.

Elena sat nursing her glass of wine when a leather-clad elbow softly nudged her arm. Reacting to the touch, she turned her head and was met with the gorgeous set of blue eyes she had ever seen. Dropping her gaze a tad lower she the man had a panty-dropping smirk on his beautiful face.

"I do believe you're the Elena Gilbert who has won over my dear friend Ric's heart in a day," the man said in a low voice.

"_Am I getting goose bumps right now? Why the fuck do I have the urge to start giggling like a schoolgirl? Shit, he's staring at me. I am nearly 23 years old, why am I acting like this is the first time I've seen an attractive man?"_

The answer to that question was that this man wasn't just attractive. He was perfection personified. He had jet-black hair, piercing blue eyes, the bone structure of a god, and of course that smile. Damn, that smile. He was fully decked out in black. Black leather jack, black V-neck, dark jeans, and black boots.

"_Oh, dear God. Come on, Elena. Speak."_

"Yep, that would be me." she said with surprising coolness.

He looked her over, all the while holding that same smirk on his face. He sat down on the stool next to her, leaned his elbow on the counter, and propped his head up on his hand. Just gazing at her.

"I'm Damon. Like I said a friend of Ric's, who probably could've introduced us if he wasn't…uh detained."

Elena glanced over to the end of the bar and sure enough there was her best friend and new friend, making out like both their mouths housed buried treasure and their tongues were trying to find it.

"Haha well that wasn't totally unexpected." Elena said while finishing off the rest of her wine.

"Would you like another glass? I was just about to order something for myself." Every word that came out of his mouth was sexy.

"_Why am I sweating right now?"_

"Yes, that would lovely, thank you."

"I'll be right back then," he said with a wink.

"_If he's going to keep winking then I might as well just jump him now. And this damn sexualness at the end of the bar isn't helping the situation at all"_

Elena got out her phone and sent a quick text to Caroline.

***Not to interrupt your intense game of tonsil hockey, but did you happen to see the walking definition of sex that I was just talking to?*******

With her phone still in hand, she glanced down the bar to see Caroline extract herself from Ric. Caroline's jaw dropped and her fingers moved at a rapid pace.

***You mean the guy standing directly behind you, looking over shoulder at your phone? LOL*******

Just as Elena read the first four words she felt hot breath tickle the back of her neck.

"_Okay, no big deal. He might not of seen what I sent."_

"So you think I'm the walking definition of sex?" Damon said with humor filled eyes as he put the fresh drinks on the table in front of them.

"_Nope, he saw it."_

"Well hahaha, ummm…" Elena struggled with a response, until she decided to go big or go home.

"Like you don't know that you're hot." she said with a brave voice that surprised the both of them.

"I just wanted to hear you say it, love." he said with a low, husky voice and another wink.

Elena was saved just in time when Ric and Caroline decided to finally join them. They were both gazing at each other like lovesick puppies. Elena took a big swig

"So Elena, looks like you met the potential non serial killer room mate I was telling you about." Ric said as he placed a friendly slap on Damon's back.

Elena spit her drink out all over the floor and started coughing ferociously.

"…y-you're the roommate?" she spit out.

"In the flesh." Damon said with a cock of his head.

"_Why didn't I connect the dots? Of course, he was the roommate! If I would've stopped gawking at the way his jeans hugged him in all the right places maybe I would have realized!"_

Between fake coughing fits, Elena said, "Um, Caroline, could you come with me to the bathroom? All this coughing is making me tear up; I need to use some of your uhhh…EYELINER! Yeah eyeliner."

"Uh, yeah, sure. Let's go." Caroline said, playing along.

The two girls maneuvered their way to the bathroom and with a slam of the door, Elena proclaimed, "He cannot move in with us!"

"What! Yes, he most certainly can. You're clearly into him, Elena. And considering ever since I first laid eyes on him, he hasn't taken his off you, I'd say the attraction is mutual."

"Jesus, Caroline! Can't you see that he's a textbook womanizer?"

"Elena, you literally just met him. How could you possibly know that?"

"Because he's too sexy to be anything else." Elena reasoned.

"Okay, well Alaric was telling me about him. He seems like an okay guy, Elena. Plus, he's loaded. See? Rent and roommate problem solved."

"I don't have any say in this do I?" Elena asked already knowing the answer.

With a bubbly laugh Caroline yelled, "SEX IN THE CITY TIME!"

"_What have I gotten myself into?"_


	3. Chapter 3

_**Five Weeks Later**_

Elena was convinced that she was going to spontaneously combust at any given moment. Damon liked to sleep naked. Damon also liked getting a little midnight snack as well and didn't feel the need to be modest. Conveniently enough, the kitchen was wear Elena worked on her book, so she always got a nice shot of Damon in all his glory.

"_Again? Really? Do I look away or be nonchalant about it? I mean, he obviously doesn't think it's a big deal. Speaking of big...NO, Elena, stop. This is exactly what he wants. Well, flustered Elena will not be making an appearance tonight. "_

"Hungry again, Damon?" Elena inquired without looking up from her laptop screen.

Stepping up behind her chair, Damon leaned in by her ear and said, "What can I say, I'm a creature of habit," walking around the table to sit opposite her he asked, "So what's your story gonna be about?"

While trying to ignore that his stare never once left her eyes and the fact that he was indeed naked still, she managed a response, "Uh, I'm not to sure yet. To be honest, I thought this would be easy. I guess just knowing I'm not writing for a school newspaper is kinda taking a toll on me. I have an extreme case of writer's block."

"_Alright, this staring is getting a little extreme too. Oh, perfect, cue the slow, sexy smirk he has forming on his face."_

Leaning across the table, he slowly pushed her laptop closed so he had a full view of her. Without even realizing it, Elena had held her breath. "I'm not a writer or anything, but in my personal experience I have found people go crazy for a good kinky romance." he said with a slow lick of his bottom lip as he got up to go back to his room.

"Good night, Elena." he called from over his shoulder. She could swear she heard him give a low chuckle as he walked away. Finally, snapping out the smutty fog he had her under, she slammed her head down on the table and sighed in frustration.

"Oh, fuck me."

**The Next Day – Damon's POV**

"So how has the whole living with two chicks been going for you." Ric inquired as he stuffed his face with a few French fries. He and Caroline had been casually seeing each other since the night in the night in the bar, and by casually seeing each other I mean fucking like bunnies every chance they got. Ric knew Damon was a loyal friend and that Caroline was in no danger of falling under his friend's charismatic spell. Elena on the other hand, was another story.

"I've got no complaints." Damon said with Cheshire cat grin. Of course, he didn't have any complaints, especially while reliving this morning's "accidental" walking into the bathroom while Elena had just stepped out of the shower. The poor girl let out the loudest yelp and dropped to the ground in a desperate attempt to cover her self with the clothes she had on before.

"Looking good, amore" he said as he extended his hand to help her up.

She swatted it away while ripping a towel off the rack and storming out of the bathroom.

"Damon, I know that look. Elena is a nice girl; please don't taint her with your sick perversions." Ric pleaded.

"I'm no pervert, Ric. I'm just fascinated with the opposite sex and their anatomy." Damon said with the most innocent of faces plastered on his face.

"Uh, okay, there Don Juan." Ric said jokingly.

"Hahaha, look man, I like Elena. I may be guilty of a few innuendos, but other than that my intentions are completely honorable." If making her scream his name and come so hard she blacks out could be considered so, then yeah, completely honorable.

"Just remember she has that book she has to work on. This is a big deal, Damon. Don't fuck it up for her by seducing her into your bed every night."

"Relax, Ric, your grays are starting to show," Damon said reclining back in his seat to get better look at the passing waitresses ass sashaying by, "I plan giving her a few good ideas, anyway."

"Yeah, that's what I'm afraid of." Ric mumbled under his breath.

**Back at home – Elena's POV**

"Oh, my GOD! Elena, he totally wants you!" Caroline screamed in glee.

"Caroline, you're not at all helping the situation. And no he does not. I'm sure he does acts like that with everyone that has a vagina."

"That very well could be true, but come on! He's gorgeous! Aren't you at all curious about what having hot, steamy sex would be like with him? Actually, I know you are, because you took his advice about the book!"

Elena had indeed taken Damon's advice and began writing her first novel, a romance novel. A kinky one.

"That doesn't mean anything, Care."

"Sure it does! OH, I have an idea! Why don't you write your experiences!"

"Pfft, what experiences? The time I lost my virginity to Matt after Prom? I'm sure the mental image of him smacking his nose off mine every time he went in for a kiss or the whole whopping five minutes the whole process lasted will make people go running for their nearest bookstores." Elena said sarcastically while rubbing her temples.

"Hell no. I wouldn't even buy that out of pity. I'm talking about your experiences with Damon!" Like it was the most normal explanation in the world, Caroline sat staring at Elena with a big accomplished smile on her face.

"We haven't had sex, Caroline!"

"Yet." Caroline said with a mischievous grin.


	4. Chapter 4

"What are you getting at, Caroline, that I have sex with Damon just to write this book? That's insane!" Elena couldn't believe what her friend was suggesting.

"Oh, knock off the Virgin Mary act, me and you both know you want to. Give in already!"

"It doesn't matter if I want to, Care! I hardly know him." Elena tried to reason.

"He's sex on two legs and he loves being naked, what else could you possibly want to know about him?" Caroline did propose a good point.

"_Maybe I should. We're two consenting adults. What could go wrong?"_

"Okay, okay, so hypothetically speaking, if I was to do this…..how do I even go about it?"

Elena had sworn off sex ever since the whole Matt debacle (it was that bad) and it left her feeling like sex was a completely foreign subject. Luckily, the infamous sex kitten herself, Caroline Forbes, was her best friend.

"Well, first things first, we need to go and get you some new lingerie." Caroline said seriously.

"Why, there's nothing wrong with mine."

"It needs to be sexier, Elena! No one wants to read a book where the girl is wearing your standard Target bra! Think about it as acting, so with that in mind, you gotta be more cool around him. Just be like 'yeah, I know you're gigantic peen is all up in my face as I'm trying to write my book, but I don't even care.' Got it?"

"Wow, Caroline, I had no idea you were such a romantic." Elena said sarcastically.

"Oh, quit stalling. Let's go get you some slutty-wear!"

**Later that night, back at home. – Damon's POV**

"There you ladies are. I thought I'd treat you two to a nice homemade dinner. Consider it a thanks for allowing me to move in with you." he said.

"Oh, Damon, you know we needed you more than you needed us." Caroline giggled.

"I beg to differ." Damon said with wink directed at Elena after looking over her entire body.

"Um, yeah, I'm just gonna put this stuff away." Elena said.

Damon smiled at the nervous tone in her voice.

A few moments later, Elena came out of her room and Damon's jaw dropped. She done away with her simple jeans and sweater combo and instead had on black spandex short shorts and a tight little tank. Was she even wearing a bra? Nope, she wasn't. It left nothing to the imagination. Her hair was thrown up in bun, which Damon loved because he got a view of her lovely slender neck; a neck that he yearned to place hot kisses all over, to claim.

"_She's trying to kill me."_

After dinner, Caroline texted Ric seeing if she could stay over his place, claiming she missed him, even though it was just a ploy to get "Operation: Delena" in affect.

"Here, let me do the dishes. You cooked, its only fair." Elena offered.

"Don't be silly, Elena. I wouldn't leave you to do it by yourself." Wink.

"Could you maybe stop doing that so much?" Elena asked exasperatedly.

"Doing what?"

"Like you don't know. You same something with a sexual undertone and then wink." Elena called him out.

"Why, is it getting to you, Elena?" he walked over to where she was both the sink and put his hands beside her, on the either side of the counter. Caging her in.

**Elena's POV**

Her breathing sped up rapidly. She could feel his body radiating off of him and into her.

"Because that's the point." He whispered into her ear, gently brushing his lips over it, eliciting a shiver from her.

"_So that's what people mean by erogenous zone. Looks I found mine."_

"Damon, what are you doing?" she asked in a last ditch effort.

"I'm doing, Elena, what I know you want. What I want." He said as he pushed his hips slightly into hers, letting her feel just how much he wanted it.

Elena bit back a moan that desperately wanted out. He was turning her on; there was no doubt about it. But she didn't want to continue this until he knew what she wanted from this.

"Damon, I want you to help me with my book." She said in a hushed tone as he was kissing her neck.

That got his attention.

"How so?" he said with a grin.

"It's going to be a romance. A highly sexual romance and-" she was cut off.

"And you want to use me so you can write a more visual novel. I get it and I'm fine with it. Now let's go." He grabbed her hand and started dragging her to his bedroom.

"Wait! You're okay with this? Just like that?" she couldn't believe how easy that was.

"Just like that. Now, can we continue this in my room?" He pleaded. He wanted her bad. It perturbed him a bit. He was never was this desperate for a woman before. If anything, they were desperate for him. But Elena was different. Why was she different?

Entering his bedroom, Damon slammed his door shut and pinned Elena against it. As much as he wanted her, he would take this slow. He knew the most important aspect of sex was making sure you're lady was just as ready as you are. And right now, Elena looked like a deer caught in headlights.

**Damon's POV**

"Elena, relax. I want to make you feel good." He said as he leaned in and placed a light kiss on her lips.

He reached up and freed her hair from the bun, watching as her chestnut locks fell freely down past her shoulders.

"Are you a virgin, Elena?"

"That's a slightly bold question, don't you think?" she asked more embarrassed then offended.

"You're shaking. It just made me wonder if you've ever been in this position before."

"What, having sex with someone just so I can write a better book? You're right, I haven't." she said with that famous Elena sarcasm.

"No, being properly fucked." He said with his head cocked to the side, studying her.

At hearing that response, Elena's eyes visibly bugged out of her head.

"I'm not a virgin. But I've only had sex once and it was absolutely terrible. I never craved to do it again after that." She said.

"Sex so bad, it made a beautiful woman swear it off. Now that's a shame," tipping her chin up so he could look into her eyes, he continued, "I promise you, Elena, after this, you'll be begging me for more." He said with complete confidence, not a trace cockiness in his tone.

Before Elena could respond he was back to kissing her neck and ear, his hands playing with the hem of her shirt.

His hot breath tickling her ear, just like the day they first met, sent her thighs in a trembling fit.

He had one hand tangled in her, the other unbuttoning his pants.

The kiss began to deepen, and it was Elena who initiated it. She reached down to the hem of his shirt and pulled up and over his head, tossing it to the floor. Seeing him in this light instead of the shitty overhead stove lighting that she usually saw him in was like breathing for the first time.

He wasn't overly muscular, but perfectly toned. She ran her fingers down his chest, relishing how she felt his muscles tensed everywhere she touched.

"Take off your shirt, Elena, I want to see you."

Eager to comply, she ripped her shirt off and threw it to land where his lay crumpled.

"Perfect." He said mesmerized as he cupped both her perky breasts. She let out a noise that sounded very close to a purr as he brushed his thumb over her nipples.

Before she could even realize it, Damon lifted her and gently laid her on his bed. Looking up she saw him removing his pants at an excruciatingly slow pace. Sensing her frustration, he smirked and stripped them off, along with his boxers.

She gulped at the sight of him aroused. Jesus, this definitely was not going to be like her first time.

Too busy staring at his hugeness; she didn't notice Damon sliding her shorts off until he told her to lift her hips.

Elena was amazed at how at ease she felt with him. It had been four years since anyone had seen her naked, but she didn't feel any skepticism about what was happening.

"You're gorgeous, Elena."

As she looked up, she saw him gazing at her with a hungry look in his eyes. He began kissing up her legs, right up to her inner thigh when he switched legs and started all over again. She couldn't handle the build up.

"Damon, please…." She begged.

That's all he needed to hear.

"Spread your legs for me, baby." He told her.

Leaning down to her hot core, he brushed his fingers over her swollen clit. "Oh…." she fisted the sheets she lay on, trying to alleviate some of the sensation. Wasting no time, Damon plunged a finger deep inside her.

"Jesus, Elena, you're so wet for me." Damon said huskily. He began slowly moving his finger in and out of her, loving how hot and wet she was.

"Fuck, Damon.." she moaned breathlessly. He looked up at her and pushed a second finger into her, watching as her face contorted with pleasure. He began working her faster until her hips would lift off the bed, in which he would gently push her back down with his other hand. All the while continuing his sinful act on her.

"Oh, my God, Damon please, let me." She begged. Know full well what she wanted, he teased her, "Let you what, Elena?" he said with his signature smirk and glistening blue eyes boring into her.

"Please, let me come!" she screamed.

"You're wish is my command." And at that he licked at her bundle of nerves and she came instantly. This time when she lifted off the bed, nothing could bring her back down.

Without a second thought, Damon reached into his nightstand and pulled a condom on. Positioning himself at her entrance, he asked, "Are you sure you want this, Elena?" As much as it pained him to ask, he didn't want her regretting this.

"Fuck me, Damon." She said in a voice that nearly made him come right then and there.

Looking down at her, he pushed himself inside her wet heat.

"Fuck, Elena, you're so tight. So wet." he groaned as quickened his pace.

She wrapped her legs around his legs tight and started moving in rhythm with his thrusts. "Harder, Damon, please…" Elena couldn't believe how good this could be. Or better yet, how good Damon was at it.

Without giving her notice, he pulled out of her and flipped onto her belly.

"Get on your hands and knees, Elena, I want to take you from behind." he growled.

She scrambled to obey and felt him thrust back into her. He was so much deeper this time. She felt him immediately hit her G-spot over and over. He gripped her shoulders and started pounding into her mercilessly when she had her second orgasm of the night.

"SHIT! DAMON!" her orgasm violently ripped through her, sending her into aftershocks with Damon still plunging deep into her, now holding both her arms behind her back and face pushed onto the bed.

"That's right, baby, come all over my dick. I love feeling you clamp down on me." He reached over her to ferociously rub her clit, sending her into another orgasm. Hearing his animalistic growl was the last thing she heard before her vision went black.

True to the promise he made himself earlier, Damon made her come so hard she blacked out.

Collapsing next to her on the bed, Damon situated her under the cover. Without a second thought, he pulled her to his chest.

Feeling how good she felt in his arms and knowing he wouldn't be able to let her go after this he breathed, "What have I gotten myself into?"


End file.
